Dasabuvir sodium monohydrateProduct ingredient for Dasabuvir

Name
Dasabuvir sodium monohydrate
Drug Entry
Dasabuvir

Dasabuvir is a direct acting antiviral medication used as part of combination therapy to treat chronic Hepatitis C, an infectious liver disease caused by infection with Hepatitis C Virus (HCV). HCV is a single-stranded RNA virus that is categorized into nine distinct genotypes, with genotype 1 being the most common in the United States, and affecting 72% of all chronic HCV patients 8. Treatment options for chronic Hepatitis C have advanced significantly since 2011, with the development of Direct Acting Antivirals (DAAs) such as Dasabuvir. Dasabuvir is a non-nucleoside NS5B inhibitor which binds to the palm domain of NS5B and induces a conformational change which renders the polymerase unable to elongate viral RNA Label. The binding sites for non-nucleoside NS5B inhibitors are poorly conserved across HCV genotypes leading to the restriction of Dasabuvir's use to genotype 1 only.

In a joint recommendation published in 2016, the American Association for the Study of Liver Diseases (AASLD) and the Infectious Diseases Society of America (IDSA) recommend Dasabuvir as first line therapy in combination with Ombitasvir, Paritaprevir, and Ritonavir for genotype 1b and with Ribavirin for genotype 1a of Hepatitis C 8. Dasabuvir, Ombitasvir, Paritaprevir, Ritonavir, and Ribavirin are used with the intent to cure, or achieve a sustained virologic response (SVR), after 12 weeks of therapy. SVR and eradication of HCV infection is associated with significant long-term health benefits including reduced liver-related damage, improved quality of life, reduced incidence of Hepatocellular Carcinoma, and reduced all-cause mortality 7.

Dasabuvir is available as a fixed dose combination product with Ombitasvir, Paritaprevir, and Ritonavir (tradename Viekira Pak) used for the treatment of chronic Hepatitis C. Approved in December 2014 by the FDA, Viekira Pak is indicated for the treatment of HCV genotype 1a with Ribavirin or genotype 1b without Ribavirin Label. When combined together, Dasabuvir Ombitasvir, Paritaprevir, and Ritonavir as the combination product Viekira Pak have been shown to achieve a SVR of 100% for genotype 1b and 89% or 95% for genotype 1a after 12 weeks or 24 weeks of treatment including Ribavirin.

Accession Number
DBSALT002711
Structure
Thumb
Synonyms
Not Available
UNII
OG6D40M62L
CAS Number
1456607-55-8
Weight
Average: 533.57
Monoisotopic: 533.15965109
Chemical Formula
C26H28N3NaO6S
InChI Key
SJHKKWUESHNTBB-UHFFFAOYSA-M
InChI
InChI=1S/C26H27N3O5S.Na.H2O/c1-26(2,3)22-15-20(29-11-10-23(30)27-25(29)31)14-21(24(22)34-4)18-7-6-17-13-19(28-35(5,32)33)9-8-16(17)12-18;;/h6-15,28H,1-5H3,(H,27,30,31);;1H2/q;+1;/p-1
IUPAC Name
sodium 3-[3-tert-butyl-5-(6-methanesulfonamidonaphthalen-2-yl)-4-methoxyphenyl]-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-1-ide hydrate
SMILES
O.[Na+].COC1=C(C=C(C=C1C(C)(C)C)N1C=CC(=O)[N-]C1=O)C1=CC2=C(C=C1)C=C(NS(C)(=O)=O)C=C2
External Links
ChemSpider
34992812
ChEMBL
CHEMBL3544985
Predicted Properties
PropertyValueSource
Water Solubility0.00119 mg/mLALOGPS
logP4.52ALOGPS
logP3.42ChemAxon
logS-5.6ALOGPS
pKa (Strongest Acidic)9.09ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area102.01 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity133.24 m3·mol-1ChemAxon
Polarizability52.82 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon